


On Your Knees (or that one time Cas and Dean had kinky sex with Betty Days)

by Eveanyn



Series: The Betty Chronicles [1]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, F/M, M/M, Multi, My First Fanfic, Plot What Plot/Porn Without Plot, Rimming, Threesome - F/M/M
Language: English
Status: Completed
Published: 2014-08-03
Updated: 2014-12-22
Packaged: 2018-02-11 13:31:05
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 14,459
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2070057
Author URL: https://archiveofourown.org/users/Eveanyn/pseuds/Eveanyn
Summary: <blockquote class="userstuff">
              <p>How the hell did you respond to someone telling you out of the blue they wanted to try out a sub kink to see if they liked it? It's not like Dean didn't love getting tied up, at the whim of a Dom, but… it was <em>Cas</em>. Cas, who wanted to try being submissive for someone, maybe down on his knees, back straight, gaze averted, waiting with open lips for what his Dom would want to give him, or take from him…</p>
            </blockquote>





	1. Meet Betty

**Author's Note:**

  * For [betts](https://archiveofourown.org/users/betts/gifts).



> So this is my first fic ever. It's for the lovely Betty Days and stars the lovely Betty Days. A conversation started on Twitter, one thing led to another, and ... here we are.

“I have contracted someone called a Dom to come over this evening,” Castiel said, taking a bite of his burger.

 

 Dean choked on his drink. “Wh—what? Cas, what the actual fuck?”

 

 “As I am only recently human, I am unsure as to what sexual preferences I may have. As an angel I was used to following orders. I thought perhaps it would be a logical place to begin having intercourse.”

 

 Sam looked back and forth between the former angel and his brother, trying not to grin at the open-mouthed shock on Dean’s face. “And that’s my cue to leave. I’ll go find another room. Far, far from here,” Sam grabbed his food and backpack and walked out the door of the motel, chuckling under his breath as he went.

 

 Dean was still staring at Cas. He had no idea where to go with this. How the hell did you respond to someone telling you out of the blue they wanted to try out a sub kink to see if they liked it? It's not like Dean didn't love getting tied up, at the whim of a Dom, but… it was _Cas_. Cas, who wanted to try being submissive for someone, maybe down on his knees, back straight, gaze averted, waiting with open lips for what his Dom would want to give him, or take from him…

 

 Dean licked his lips and finally managed to look away. “What time is—she?—coming over?” he asked gruffly.

 

 “I am expecting her to be here within a half hour. I understand if you wish for me to meet her outside and move somewhere else for this experience. I do not wish to make you uncomfortable.”

 

  _It’s a little fucking late for that_. Dean shifted in his chair, trying to will away the tightness in his jeans and pretending it was from the thought of a female Dom coming into his hotel room. “No, man, I’m not going to let you go meet up with some Dom without screening her first,” God, he needed a drink right now. He got a beer out of the fridge and downed half of it in one go.

 

 “She seems like a lovely young lady. We have corresponded many times and I sense no deceit in her. I believe you will like her. She has answered all my questions fully and wanted to make sure that I am comfortable with the ‘scene’ she said she wanted me to ‘play’ with her.”

 

 Dean grunted a response, his stomach churning. Cas’ first sexual experience was going to be with a Dom. He didn’t want to imagine anyone playing out a scene with Cas. He didn’t want to think about how someone else’s hand would look wrapped in that hair, guiding his head down as he licked and sucked and—

 

  Dean finished his beer and got another from the fridge, wishing it were whiskey. He would have to go out as soon as Cas left, get really drunk, maybe pick up a girl. Or two. Anything to keep him thinking about what someone else’s hands would be doing to the man who was walking up to him, not stopping until he was way too far into Dean’s personal bubble.

 “Dean,” he began.

 

 “What, Cas?” They looked at each other, both tense, breathing tightly. Castiel frowned, eyes searching Dean’s, and opened his mouth again.

 

 Whatever he was about to say was cut off with three sharp raps on the door. Dean took a step back and exhaled heavily, walking over to answer it. He looked through the peephole. There was a woman standing there, of average height, with bright red hair and a luscious, curvy body. No. It couldn’t be. Dean opened the door.

 

 And stared.

 

 It was her.

 

“Betty,” he breathed out, stepping back automatically.

 

Betty walked into the room, surprise on her face at seeing Dean. She closed the door and touched his cheek. He leaned into her hand and closed his eyes, breath coming out in a small shudder. “Dean. It’s been a long time. I wasn’t expecting you.”

 

“I wasn’t expecting _you_. Cas just told me that he contracted a Dom and that she was coming over tonight.” His voice had gone soft and low, his eyes dark.

 

Betty patted his cheek one more time before she turned to take in the rest of the room, and Cas. “And you must be Castiel. Look at you.” She glided over to Cas and cupped his face in her hands. “You are just breathtaking. But you should have told me that you wanted someone else to join us tonight. I would have planned out our scene a bit differently. Or is he just watching?”

 

Cas’ eyes flew to Dean, then back to Betty, alarmed. “I had intended on us being alone,” he began, then stopped, his cheeks turning pink.

 

Betty took a step back, looking between the two men. “So, you two are not together?” When Cas shook his head and Dean stared a hole in the floor, she grinned. “That’s okay. I think I know how we can still make this fun. Castiel, darling, would you mind if we amended our contract for this evening to add in Dean?”

 

The blood drained from Dean’s face. He sputtered. “Now, hold on just a damned minute. You’re putting the cart way before the fucking horse. There’s no way I would—” he began, then stopped abruptly when Betty held up a hand to him.

 

“Dean, please. There’s no need to play games with me. I can see that you would enjoy this. No,” she spoke right over him when he opened his mouth again to protest, her voice going sharp, “do not lie to me, even if you are lying to yourself.” She paused, letting her words sink in. Dean shifted, but kept eye contact with her as he knew she’d want. She smiled. “Good boy. Now, if Castiel is amenable, would you join us this evening?”

 

Dean exhaled sharply, cutting a look at Cas. He was standing there, looking between Betty and Dean with his head tilted and a confused expression on his face. But his cheeks were flushed and Dean could have sworn he saw _want_ in the former angel’s eyes. His chest clenched and the hot feeling in his groin that he’d always tried to pretend wasn’t because of those damned blue eyes flared up. This would possibly be the only opportunity he’d have where he could be near Cas like this and it would be okay. He shouldn’t say yes. He shouldn’t give in to this. He should just turn around and walk the fuck out the door and get blackout drunk. Instead he stood there, breathing hard, trying not to see the way Cas was looking at him. Trying not to imagine what sounds Cas would make later, regardless of whether or not Dean was present. Damn it, he wanted to hear those sounds. He wanted to be the one to elicit them. Dean _wanted_.

 

He looked back at Betty, nodded once, jaw tight. She quirked an eyebrow at him before turning back to Cas. “And you, darling? Are you in agreement?”

 

“I don’t understand. How do you two know each other?”

 

Betty chuckled, bright red lips curving into a smile. “Oh, you really are new at this, aren’t you? Dean was my sub for almost two years.”

 

Cas looked at Dean, who was trying very hard to memorize the pattern in the carpet. “Dean? Why didn’t you tell me this?”

 

“It’s, uh … it’s not something I’ve ever told anyone, Cas.” He rubbed the back of his neck. “It was a long time ago. Right after Sammy went off to college.”

 

Castiel nodded after a moment, turned back to Betty. “I see no reason that the contract should not be amended.”

 

Betty grinned. “Excellent. Now—”

 

“Hold on a second, please, Betty. Cas, can I, uh, talk to you?” Dean was still looking at the floor.

 

“Of course, Dean. What is it?”

 

“…Privately?”

 

Betty chuckled. “I’ll go and get the contract from my car. I’ll give you three minutes.” She walked past Dean, patting his ass as she went, and closed the door behind her.

 

Dean shifted uncomfortably. “Are you… Cas, are you sure you want to do this? I mean—hell, I don’t know what I mean. I’m confused as shit right now, buddy.”

 

Cas walked into Dean’s personal space again and put a hand on his shoulder. “Dean, I am not uncomfortable with this situation. I understand that you have had many sexual partners and therefore a great deal of knowledge that I could learn from, and given that Betty is a former lover of yours, I find myself looking forward to this encounter even more than I was when I contracted her.”

 

Dean’s heart stuttered. Like a fucking teenager. Jesus, he was pathetic. “Um, why?”

 

Cas gave him a look Dean was sure he learned from Sam. “You already have a dominant/submissive relationship with Betty. I can learn from both of you now and see if this is something I would enjoy doing again. It will be much easier when there are two of you who understand this dynamic from experience.”

 

_Oh_. Dean tried to not let any disappointment show. “Uh, yeah. Okay. Um. So. Did she tell you the basics about being a sub?”

 

There was the Sam face again. “Yes, Dean. I also read some things on the internet. I am not unfamiliar with the concept, and she said that we would start very slow this first session, and if I was interested in continuing we would move on to more ‘intense’ scenes, as she put it. Apparently this type of relationship is to be built around trust, and things get more involved as a relationship is established. While I do not yet know Betty enough to give her my full trust, I do trust you, Dean. I will be able to enjoy this more with you here.”

 

Before Dean could process that, Betty breezed through the door carrying a black messenger bag. “All right, my darlings. Time’s up. Let’s go over this quickly before we get started.” She pulled out a folder. “Dean, have any of your preferences or hard limits changed since we last saw one another?” Dean shook his head. “Good. Has your safeword changed?” He shook his head again. “All right, then. Castiel, would you like to add anything to your hard or soft limits now that Dean will be joining us?” At his negative reply, she grinned, then grabbed up the messenger bag again, handing it to Dean and walking towards the bathroom. “Excellent. Now, I will go into the bathroom and allow you both to get into your headspace. One of you open the door when you’re ready for me, then I want both of you kneeling at the foot of the bed. Dean, be a dear and set up.” With a click of the door the two men were alone again.

 

Dean cleared his throat and instead of thinking about what was going to happen he busied himself with pulling items out of the messenger bag and setting them on the nightstand. A bottle of lube. Condoms. A vibrator. Some rope. A shiver of anticipation ran up Dean’s spine as he pulled the last item out of the bag—a butt plug. _Oh, god._ Betty always had liked to tease, to build the anticipation within Dean: _will we use this or won’t we?_ Sometimes she used more toys in a single scene than he knew she could find use for, and sometimes she would set out objects, letting Dean fantasize over them while never letting him touch them.

 

He arranged the items in the precise way Betty had taught him. It was familiar, grounding. When there was nothing else for him to do, Dean turned around to find Cas already kneeling patiently by the foot of the bed, back straight, head upright, eyes staring forward, hands behind his back. His goddamned mouth was parted slightly, exactly as Dean pictured it. He suppressed the urge to drop down in front of the other man and devour his mouth, pushing his tongue inside to taste what no one else had. Instead he asked quietly, “Are you ready?” When Cas nodded once, Dean walked slowly towards the bathroom. He paused with his hand on the knob and, taking a deep breath and telling himself to quit being such a fucking pansy, opened the door. Without looking in, he turned back towards the bed and knelt next to Cas, mimicking his posture.

 

Anticipation flowed through Dean at the thought of doing this again. He could be good. He could show Cas how to be good.

 

Betty walked in and went straight to the nightstand to inspect the items she’d brought. “Well done, Dean. You remembered.” Dean sat up a little straighter, flushing slightly at the compliment.

 

She moved in front of the two men kneeling at the foot of the bed and stopped, admiring them. “Oh, my good boys. Look at you, sitting just how I want you, waiting for me.” She ran a hand through Cas’ hair and smiled at his indrawn breath. His eyes stayed fixed on the wall opposite him. “Already so good,” she whispered, leaning down and planting a soft kiss to his lips.

 

Dean couldn’t help the choked sound that came from his mouth. Betty paused, looked at Dean. “Well now. That’s interesting.” She considered him for a moment. “Dean, turn towards me. Watch.” As he obeyed Betty knelt so she was on the same level as Castiel. She pushed both her hands back into his hair and tugged slightly, angling his head how she wanted it before bringing their lips together again. Her tongue languidly slipped inside of Cas’ and she explored his mouth. She pushed down on his shoulders until Cas was sitting back on his heels, then crawled on top of him without breaking the contact of their mouths.

 

A low growl escaped Dean. He was instantly hard, just from watching this. It took so much effort to stay still, to show Betty he could be good so she’d be pleased with him, maybe reward him. His eyes devoured the scene in front of him. He watched hungrily as Betty’s hands moved from Cas’ shoulders up to his throat and under the collar of his button-down. He wondered if the tanned skin there would be soft, if it would smell like Dean’s body wash. He wondered what it would taste like if he were to press open-mouthed kisses along Cas’ neck like Betty was doing.  

 

Castiel’s breath was coming in hard rasps already. His head was thrown back, eyes closed, little moans escaping his open lips. He rolled his hips up into Betty. She took her mouth away from his neck and grabbed the back of his head. “Look at me.” When he didn’t obey immediately she slapped his face. “Look at me.” His eyes flew open, meeting hers. She smiled. “Good boy. Now tell me,” Betty grinned wickedly, moving a hand down between them to cup Castiel, “Do you want this?”

 

He arched into her hand, looking for friction. Dean swore under his breath when Cas moaned out a ‘yes’.

 

“I know you do, sweet boy. But you won’t get it until you beg for it.” Betty removed her hand and stood up primly, smoothing her hands down the length of the pencil skirt she was wearing. Dean blinked. It was the first time he noticed her clothes. She was in a business power suit, which was definitely at odds with the Betty he knew. For a moment it took him out of his head, wondering why she wasn’t wearing the rockabilly-style dresses he was used to seeing her wear.

 

“Dean.” Her voice was low, purring. “Come here.”

 

Dean stumbled to his feet, keeping his hands behind his back, left hand clasping his right wrist. He moved so he was close enough that he could feel the body heat coming off of Betty in waves. It was something he’d always loved about her; she always felt like she was made of fire, that she’d burn him if he touched her for too long.

 

“Undress me. Slowly.”

 

Dean didn’t need to be told twice. He turned her towards him gently and placed a soft kiss on her lips. His hands skirted up her sides and under jacket, peeling it gently off her shoulders. He stopped before it slipped off her arms and mouthed at her collarbone, planting soft kisses. Pushing the jacket the rest of the way off, he moved his hands to the buttons of her shirt. He took his time with each one, kissing each new bit of exposed flesh as he went. When he reached her navel he stopped, gently circling it with his tongue before pushing in. Betty gasped, hands going to Dean’s head and jerking him back up. She brought their mouths together hungrily. “So good for me, Dean,” she whispered, stroking his face once before letting him resume his work.

 

Her shirt quickly followed the jacket on the floor and Dean brushed his fingertips down Betty’s arms. She shivered. Dean smiled, glad he remembered how she loved to be teased with light touches first, how she loved to let the pressure build until they were both exploding with need before giving in. He stepped in close, pressing his chest into her and bringing his hands around to the base of her neck, fingertips just barely grazing the skin. He moved his hands down in slow circles, feeling Betty’s skin quiver beneath him and her breath catch. He flattened out his hands at the base of her spine, just below the dimples that he used to spend so much time sucking on. He slowly pulled down the zipper, pushing the skirt to the floor as his teeth moved to graze her shoulder. He gently bit and sucked on her shoulder as he undid her bra and let it follow everything else to the floor. His fingertips grazed her collarbone and moved down over the swell of her breasts, moving around to cup them gently before flicking the tip of his tongue over each nipple.

 

Betty arched into his mouth. “Yes, Dean,” she whispered. He rolled a nipple between his lips as she dug her fingernails into his shoulders.

 

“You’re more beautiful than I remembered, Betty,” Dean nuzzled into her neck as his fingers danced underneath the line of her panties.

 

Just when Dean’s fingers were dipping lower, Cas shifted, hips moving forward slightly of their own accord. Betty pulled back, raised an eyebrow at him. “Castiel, do you know how to remain still?” He froze, eyes wide and uncertain.

 

Betty huffed a small sigh and grabbed Cas firmly by the back of the neck, shaking him a little. “I asked you a question. I expect an answer.”

 

“Yes. I know how to remain still.” His voice came out in a rasp.

 

“Do you? I’m not so sure. I think Dean should show you.” Betty moved towards the bed, laid at the head after propping up some pillows to make herself comfortable. “Dean.”

 

Dean turned towards her immediately, hands going automatically behind his back, left hand clasping right wrist. “Yes, ma’am?”

 

“I want you to stand very, very still for me. Only move what is moved for you. Castiel. Undress Dean.”

 

Dean’s mouth went dry and his heart pounded. He hadn’t considered that Betty would make them interact with each other. He should have known, though. His eyes were locked on Castiel’s, waiting to see what the other man would do.

 

Cas stood up and moved very slowly to stand in front of Dean. After searching Dean’s eyes for a moment, he reached out and grabbed both of Dean’s arms, turning them so Betty would be able to watch. Dean moved only insofar as Cas turned him, green eyes burning into blue. Dean didn’t think it was possible to be this keyed up, to be this full of anticipation and remain still. With Cas’ body heat so close to him, with _Cas_ reaching out to touch him, it would take every ounce of self-control Dean had to not move. He doubted he would get anything close to what he wanted if he _did_ move, though, so he gritted his teeth and kept still.

 

Cas gently pushed the flannel off Dean’s shoulders, then took his hands and brought them above his head. Cas’ fingers skimmed under the hem of Dean’s t-shirt before it, too, came off. Dean kept his arms raised above him while Cas stared at his chest, tongue peeking out to lick his full lips.

A soft groan escaped Dean’s lips and Cas’ eyes flew up to meet his. “Do you—am I doing this wrong, Dean?” His voice was like a good whiskey, burning Dean from the inside.

 

Dean couldn’t speak. Hell, he didn’t know if he was allowed to speak, and he would have had to move his head to be able to gauge Betty’s reaction. So he remained motionless, saying nothing.

 

“He won’t answer you, Castiel. Not until I tell him to. But look at that pretty flush running up his neck. I’d say you’re doing rather well. Except,” Betty’s voice dropped low, “you’re not doing quite enough. I want you to make it very difficult for him to hold still. Remember those fantasies you told me about? Pick one. Play it out.”

 

Dean’s stomach clenched. Fantasies? _Cas_ had sexual fantasies? He told them to Betty? They involved _Dean?_ His dick pushed so hard against his jeans he was sure it was going to break the zipper.

 

Cas made a choked sound, clearly torn. He hadn’t looked away from Dean, and his pupils were blown wide, want warring with whatever had kept him from enacting these fantasies long ago—most likely his fear of Dean’s reaction. “I don’t know if I can.”

 

Betty got off the bed and moved behind Castiel. She brought her lips up to Cas’ ear, tongue flicking the shell. “You’re doing so well, Castiel. Dean has his safeword. If he doesn’t wish to continue he needs only to say so.” She turned her round, beautiful face to Dean. “But you won’t, will you, Dean? You want this,” Dean closed his eyes, finally gave into the feelings he’d had for years, and nodded once. “Say what you want, Dean. Out loud for the whole class.”

 

He took a shuddering breath, then opened his eyes and stared at Cas. “You.”

 

Cas stared at Dean a moment, then something let loose inside him. He grabbed Dean’s head and yanked him in for a kiss, tongue plunging inside the other man’s mouth. Dean groaned into him as Cas moved their bodies so they were pressed together. Dean rolled his hips into Cas and yelped when a firm smack landed on his ass.

 

“I told you not to move, Dean,” Betty warned. Dean whined, but held himself still. She moved behind him, ran her hands down his back then wrapped around him, undoing his belt. “Good boy.”

 

Cas broke the kiss and moved down Dean’s neck, tongued along his collarbone, and sucked on his tattoo. Dean bit his lip, the pain from his arms still being in the air mixing with the pleasure of Cas’ mouth on him, and Betty unbuttoning his pants.

 

Betty pulled Dean back from Cas and pushed him towards the bed. She finished unzipping his pants and motioned for him to take them off himself. He did, breathing a sigh as the feeling moved back into his arms.

 

When he was fully naked Betty looked him up and down, eyes lingering on the pre-come slowly dripping out of his cock. “Look at you, practically shaking with need. Who’s gotten you so wound up, Dean?”

 

Dean scoffed and raised an eyebrow at her before he could check himself and earned a hard slap across the face. “Do not forget yourself.”

 

“I’m sorry, ma’am. It’s…everything. Seeing you again. Subbing. Cas.”

Betty smiled, a wicked gleam in her eye. “Castiel, undress yourself. Keep eye contact with Dean. You, my sweet, will talk. When was the last time you got off?”

 

“Yesterday,” Dean’s reply was immediate.

 

“And what did you think about?”

 

Deep breath. “Cas,”

 

Castiel paused at that, his shirt hanging off his shoulders, exposing his tan, well-muscled torso. Goddamn, he looked better than anything Dean’s imagination had come up with.

 

“Tell me about it.”

 

“Uh, he…he pushed me against the wall of the shower. And he … um, went down on me. And…” Dean took another deep breath, still holding Cas’ eyes. It was so fucking hot watching him undress himself while listening to Dean’s fantasies about him.

 

“Did he fuck you, Dean? Did he put his fingers in you, open you up nice and slow, until you were begging to be fucked against the wall like a whore? Did he shove himself inside you, ride you until you came all over him?”

 

Dean clenched his fists at his sides to keep from grabbing his cock. “Oh, god. Yes. And he—he marked me.”

 

“I’ll bet you loved that, didn’t you? Always were one to need that physical reminder that you were wanted. You want him to prove he wants you? Do you want him to mark you now?”

 

“Yes. Please, ma’am.”

 

Betty smiled. “I like it when you say please. Not yet, though. It’s my turn to have some fun.” She got back on the bed, laying as she had before. “I want you to tell Castiel how to please me. I want his hands on me, his mouth doing exactly what you tell him to do. You may do what you want, Dean, but neither of you may come.”

 

Cas, now fully naked, looked to Dean. They were both hard and it took Dean a moment to tear his eyes away from Cas’ cock and motion Cas onto the bed. Dean crawled up next to him and positioned Cas between Betty’s legs. He pulled down her panties and threw them to the floor somewhere behind them.

 

“Lay down on your stomach, Cas, and, uh, start by kissing up the inside of her thighs. She likes soft touches and—shit,” Dean watched as Cas began doing exactly as he asked, hands skimming up Betty’s thighs, followed by his mouth. He barely pressed his lips in, then followed it with a flick of his tongue. It took all uncertainty out of Dean.

 

“Jesus. Cas, you look so fucking sexy when you do that. Wanna watch you make her come. Put two fingers inside of her, like this,” Dean took Cas’ hand, turned his palm up, and watched as the former angel’s fingers disappeared inside Betty. She moaned and arched her hips, looking for more. “Yeah, baby, just like that. Put your mouth on her, right here,” he brushed his fingers lightly across her clit. Dean didn’t have a chance to move his fingers away before Cas’ mouth was there, covering both Dean’s hand and Betty’s clit. He sucked.

 

“Fuck. Cas, Jesus, where have you been hiding this shit?” Dean pushed his fingers further into Cas’ mouth, getting them thoroughly wet. He took them out and moved them up to Betty’s nipple, teasing. “You have to suck her nice and slow, twirl your tongue around. Just like I want to do to your cock.”

 

Cas lost his rhythm at that, fingers pausing before redoubling their effort, pushing up against Betty, seeking deeper, knowing his fingers weren’t what she craved. Dean’s dick twitched. “You like that thought? You want me to pull your cock into my mouth, want me to suck you off? God, I want that. I want it so bad, baby. You have no idea. Wanted you for so long.” Cas groaned, his mouth working against Betty until she was writhing on the sheets, her hands firmly in Cas’ hair. “You’re gonna make her come, Cas. Keep going. Don’t stop now.” Dean climbed behind Cas and laid over his back, cock slotted against his ass, his chest flush against the other man, his lips nibbling along Cas’ ear, whispering encouragement and obscenities.

 

He slowly rocked his hips forward, feeling the drag of his cock against the cleft of Cas’ ass, and groaned. “Come on, angel, make her come. I want to watch you make her fall apart.”

 

Betty was trembling, body arched up off the bed, hands pulling Cas’ hair to the point of pain. “Yes! Yes, good, so close, almost there, don’t stop, don’t stop, _don’tstopdon’tstopsogooddon’tstop_ —aah!” She went rigid for a moment, body clenching around Castiel’s fingers before collapsing back onto the pillow with a sigh. Her hands threaded through his hair gently now, stroking softly. “Good boy. So good for me. I think it’s time you got your reward.”

 

Castiel pulled his fingers out slowly, looking at Betty for instruction. She took his hand and put it in her mouth, sucking the taste of herself off his fingers. “No wonder you were so enthusiastic. I taste _good_ ,” she grinned.

 

Betty moved off the bed and contemplated the nightstand. “Dean, lay down, on your back.” He reluctantly withdrew from on top of Cas and did as he was commanded. When he saw Betty pick up the rope he moved his hands automatically above his head, earning him a fond stroke on the cheek. “Look at you. Keep up this good work and I might let you get me off, too. It’s been a while since I’ve had a nice cock in me.” She winked and bent to work, tying one end of the rope around Dean’s wrists and wrapping the other securely around a slat in the headboard. When she was finished she put everything else next to them on the bed and climbed on to Dean’s stomach, facing Cas.

 

“Now you’re going to use those glorious hands to open him up.”

 

Cas frowned. “I don’t understand what you mean.”

 

Betty gave a throaty chuckle. “Oh, you sweet boy. You weren’t kidding about your inexperience. I mean, stretch him out to get ready for your cock. Don’t worry, I’ll help you through it. Hands like that were meant to slip inside and open someone up. Here,” she popped the top on the lube, drizzled a healthy amount onto Cas’ fingers. “Start slowly, with one finger.” She took his hand and moved it between Dean’s legs. Dean bent his knees to give Cas better access, groaned when his finger made contact. “Rub slowly around the entrance, like this,” Betty lubed up her own finger and demonstrated. Dean bucked his hips at the sensation coming from two places at once. “Now slip inside.”

 

Dean hissed at the burn, reveled in it. It had been so long since he’d done this with anyone but himself. It was even better that he knew this was _Cas_ who was doing this to him. He moved, trying to get more of Cas’ finger inside him, but stopped at a sharp word from Betty. She didn’t stop her own finger from continuing to tease him, though.

 

Soon Betty told Cas to add another finger. God, it felt good. Dean tried to keep still, knowing that Betty would have no qualms about stopping if he disobeyed, would keep him from coming at all tonight. He would be left trussed up in the corner with a vibrator shoved up his ass on low, watching Betty and Cas fuck and not having enough friction to do anything about his own release. He’d had a similar experience with her before. He didn’t want that to happen, so he remained still. She didn’t tell him to be quiet, though.

 

“So good, Cas, you feel so good. Want you to fuck me. Want it so bad. I’ve wanted you for fucking _years_ , Cas.” He groaned when another finger joined the first two. Then he paused. That wasn’t Cas’ finger. Betty had slipped inside him, too. They were fingering him open together. “Fuck, that’s hot,” he whispered, clenching his hands into fists.

 

“Didn’t want you to forget about me, handsome,” Betty’s voice was low and pleased at the sounds Dean was making.

 

He heard the familiar tear of a condom wrapper and his anticipation built. Finally, he would get to feel Cas inside him.

 

He was confused when he felt the condom being rolled down his own dick. It soon melted away, though, when Betty took him into her and started a slow, agonizing rhythm.

 

“He’s ready, Castiel.” Dean whined as the fingers pulled out of him—he actually _whined_ —but a moment after he heard the lid of the lube click again he felt something much larger than a finger nudge at his entrance.

 

Cas had been nearly silent the entire time he was working Dean open, but as the tip of his cock pushed past that first tight ring of muscle Cas let out a loud, guttural moan. “Oh, god, Dean,” he whispered, his voice breaking. He moved again, hands clenching Dean’s thighs. Slowly, so slowly, too slowly for Dean, Cas pushed inside him until he couldn’t go any deeper. “ _Dean,_ ” was all he said.

 

“I know, Cas. I know,” Dean whispered back, chest tight.

 

Betty leaned forward a little and grabbed Cas’ neck, kissed him sweetly on the mouth. “Move. Watch me, watch him. Fuck him as he’s fucking me. After I come again you both have permission to come.” Dean took that as his own permission to move. He rolled his hips up and into Betty, then slammed himself down hard onto Cas’ cock. Betty’s breath caught in her throat and her hand moved down between her legs, rubbing her clit, while the other moved up to pinch her nipple. “That’s right, Castiel,” she murmured. “Drive into him. Fuck him. Take him apart. Shove your cock into him while I ride him. Fill him up. Make him come.”

 

Castiel’s hips stuttered at that, and he felt an unfamiliar coiling in his abdomen. He thought he knew what that might mean, so he slowed his pace and concentrated on breathing evenly.

 

Betty didn’t slow her pace, though. She slammed up and down onto Dean’s cock, rubbing her clit at a frantic pace, exhaling breathy moans.

 

Dean choked on a cry. “Please, ma’am,” was all he said. Betty loved it when he was good for her. It pushed her over the edge. She came for the second time, riding out her orgasm, her walls clenching around Dean. She didn’t waste any time coming down from her high, sensing that the two men needed to finish this with just each other, so she climbed off Dean and moved to sit on the other bed, watching them hungrily. She loved watching.

 

With Betty no longer between them, Cas crawled up the bed so he was lying right on top of Dean. He sucked into Dean’s neck, hard. Dean knew he’d have marks in the morning, proof that Castiel had wanted Dean like this. Cas reached up and untied Dean’s hands. They immediately went around Cas’ neck and Dean pulled him in for a kiss.

 

“Fuck, Cas,” Dean mumbled against his mouth, “I need this, need you. Want to make you come, too. Jesus, I’ve waited so long to do this. Come for me, angel. Come with me, please.”

  
Cas moaned into Dean’s mouth, snapped his hips forward forcefully. As he hit Dean’s prostate his eyes fluttered closed and he moaned. Cas did it again. And again. With a final thrust and a desperate, “Dean,” Cas came, spurting hot inside him.

 

That was all it took for Dean to come, too, untouched and shouting Cas’ name.

 

Castiel collapsed on top of Dean, his head going in the crook of his neck. He breathed in the scent of sex and sweat and _Dean_ , a scent he’d been familiar with for years but had never thought to be able to encounter this close. It was even better when Dean wrapped his arms around him.

 

Betty chuckled. “Well, Castiel, I’m guessing thanks are in order. Looks like this was a long time coming.”

 

Cas hummed, not moving. He heard Betty putter around the room and the sound of water running for a moment. He protested when Dean’s arms were taken away from him. “Relax. I’m cleaning you off. You can go back to cuddling in a minute,” Betty’s voice was fond, and Dean and Cas let themselves be wiped off. Castiel slid down next to Dean, keeping one arm wrapped around his chest and a leg nudged between both of Dean’s.

 

Betty pulled on the scratchy motel bathrobe and sat at the head of the bed, fingers idly threading through Dean’s hair. Dean shifted himself and Cas over so there was room for Betty to lay her head on Dean’s left shoulder. “I’m sure you two have a lot to talk about, so I won’t stay much longer unless you ask me to. However, I need to know how you’re doing, especially seeing as this is Castiel’s first experience.”

 

Castiel opened his eyes and looked over at Betty. “I am fine. It was a lovely experience,” Betty snorted. Cas frowned. “I do not know that submission in a sexual relationship is something I would like to continue, though. I thought that it would be a natural progression for me, but I am unsure now.”

 

Dean tightened his arms around Cas, a small grin on his face. “Yeah, pretty sure you’d make a great Dom, though.”

 

Betty cocked an eyebrow at them. “I think I’d agree. Castiel, if you’re interested, I’m more than happy to meet with you, give you some tips, help you get started. You probably couldn’t ask for a better sub than Dean.” Dean flushed. Betty kissed his cheek fondly.

 

Castiel nodded. “I think I’d like that. That is,” he paused, looked at Dean almost shyly, “that is, if you would be …amenable, to continuing our physical relationship.”

 

Dean laughed. “There’s no way I’m giving you up now.” He kissed the top of Cas’ head and tucked it back onto his shoulder.

Betty stood. “Well, then, my darlings, I think this is where I excuse myself. I’ll leave my number. If either one of you needs anything, you call me. I will call Castiel tomorrow to check on you.” She quickly gathered everything into the messenger bag, then stooped and gave each of them a fond kiss. “If only I were the type of girl to fall in love with guys. Neither of you would stand a chance.”

 

Dean smiled. “Thank you for this, Betty. Really. I don’t know if I’d have ever done this without you.”

 

She patted his cheek fondly. “Of course, my sweet boy. Don’t wait this many years before seeing me again.”  
  
“You bet.”

 

Betty grinned at them, raised her eyebrows suggestively. “I hope I’m interrupting tomorrow when I call.” She winked. “Laters.” Still in the motel’s bathrobe, she walked out the door.

 

Cas snuggled his head closer into Dean’s chest as Dean maneuvered the blankets up and over them. There would be time later to talk, to have the inevitable chick flick moment, but for now, Dean concentrated on the solid weight of the former angel next to him, his breathing slow and even. He slid his hand down to Cas’ and twined their fingers together. Pressing a soft kiss to his forehead, he closed his eyes and drifted off into sleep.


	2. Chapter 2

**Summary for the Chapter:**

> Smut and Fluff

**Notes for the Chapter:**

> So I'm REALLY sorry it took me this long to get a freaking update for this! For some reason this chapter did NOT want to be written. It's still a little rough, I think, but there's only so many hours I can stand staring at this before I decide I'm just making myself crazy. 
> 
> It's un-beta'd, so please point out any major errors because all mistakes are mine.
> 
> Some of you may notice something stolen directly from Sex 101. It was used with Betty's permission.
> 
> Anyway. Without further ado, Chapter Two.

Dean woke to the feeling of a warm, heavy body draped over him. It had been a while since he’d woken up next to anyone. He was about to quietly get out from under the still-sleeping body to make his escape when his brain finally clicked, reminding him exactly _who_ the sleeping form was.

 _Oh_.

Dean kept still with his eyes closed. He waited for the inevitable freak-out, the urge to get up and run as far away as he could. He was almost surprised when it didn’t come. Sure, he’d told Cas last night that he definitely wanted to continue their physical relationship—and god, did he—but Dean had always been good at pushing away his feelings for Cas. He wasn’t sure that he’d be able to keep them shoved into the locked box in the recesses of his mind where they were normally kept if he was able to touch the other man whenever he wanted. That meant vulnerability. But, shit, wasn’t he already vulnerable when it came to Cas? Would it hurt for him to actually _enjoy_ himself for once, give in to what he’d been denying himself for so long?

Dean’s musings were interrupted by the sound of the door opening. He squinted his eyes against the glare of the morning sun, vaguely making out the shape of his sasquatch-sized brother coming through the door.

Sam paused partially in the doorway, making sure he wasn’t interrupting. When he didn’t see anything that would scar him for life, he stepped all the way in the room, kicking the door closed with his foot. He set a giant bag that smelled like breakfast down on the table and made his way over to the unoccupied bed. After sitting awkwardly for a minute, he finally gestured at Dean.

“About fucking time, dude. It only took you how many years?”

Still twined around Cas, Dean flipped him off. “Shut it, Sammy.”

“Jerk.”

“Bitch.”

Sam smiled. “Well, I’m happy for you, anyway. But, uh, pretty sure you two are going to be impossible to be around for the next … I don’t know, while. I found a case over in Indiana that I’m going to go check out. I’ll give you two some space. Just wanted to let you know before I took off.”

Dean extricated himself from Cas, careful not to wake the other man. He started to pull back the covers to give Sammy a hug, then realized that both he and Cas were still completely naked. He tugged the blanket around himself sheepishly. “Uh, sorry. You be careful, Sammy. You call me if you need anything.”

Sam took a deep breath, obviously debating, then carefully went in for a hug, making sure he didn’t touch anything below the shoulders. “I will, Dean. You be good to him. Be good to yourself for once.”

Dean looked over at Cas’ sleeping form and smiled. “Yeah, Sammy. I think I will.”

Sam studied Dean for another moment before nodding. He got up and gave a half-wave before gently shutting the door behind him.

Dean deliberated for a moment, staring between the enticing jaw line of his still-sleeping former angel and the bag of what had to be pancakes and bacon. With one last, longing look at breakfast, he crawled back under the covers. It was time to satiate his other hunger.

With feather-light touches, he stroked his way down Cas’ arm and gently nipped at his jaw. When Cas stirred, he moved his hand lower, down his abdomen and settling on a hip bone, thumb moving back and forth across it gently.

Dean moved closer, pressing his growing erection into Cas’ thigh and rutting into it slowly. “Good morning, angel,” he whispered, inhaling the scent he’d grown so attached to over the years.

Castiel frowned sleepily. “Dean, I am no longer an angel.”

“I know, but you’re still _my_ angel.” He kissed his way across Cas’ face, then took his mouth sweetly. Dean rarely had an opportunity to be sweet.

A moan caught at the back of Cas’ throat as their lips explored each other. Hands roamed as mouths became more heated. When Dean’s hips pushed against his again, bringing their erections together, Cas broke the kiss, gasping. “Dean,” he whispered. “Please, I need you.”

Dean rolled them until he was lying on top. “You’ve got me, sweetheart. I’m right here.” He ground their hips together, loving the little noises he was eliciting from the other man. Castiel had been relatively quiet the night before, and Dean wanted to see if he could change that. “I wanna make you feel good, Cas. What do you want?”

Castiel shook his head, eyes closed. Dean stopped moving and pulled back a little. “What, Cas? Do you want me to stop?”

Those damned blue eyes snapped open and met his. “No. No, I just…I’m not very familiar yet with the intricacies of intercourse, so I am unaware of what would be sexually gratifying to me. Please do what you want with me.”

Dean stared at him for a long while. He could hardly believe the trust he was being given, no questions asked. It was simultaneously humbling and incredibly arousing. “Okay. But you’ve gotta tell me if you don’t like it, and I’ll stop.”

“My safeword is Impala.”

Wait. “What? Why?”

“Betty told me to pick a word that made me feel safe. I associate your car with you. It makes me feel safe. What’s your safeword?”

“Nickelback.”

Cas tilted his head, eyes narrowed. “What is a nickelback? Is it some type of gorilla?”

Dean laughed. “No, it’s the name of a really shitty band. I picked it because it was the first thing I thought of when I really wanted something to stop.”

“Oh.”

There was a pause, then Dean leaned down and slowly kissed Cas. “But I don’t want this to stop. Do you?”

Castiel shook his head, hands moving up to tangle themselves in Dean’s hair.

“Good. Then let me take care of you, Cas. I want to make you come.” Castiel whimpered, making Dean wonder if dirty talk was something that got the former angel going. He sat up, legs on either side of Cas’ hips. “Do you want that, Cas? You want me to make you come? ‘Cause I’ve got to tell you, I’ve been waiting for fucking _years_ to get my mouth on your cock.”

Castiel’s hips involuntarily pushed upward, seeking relief. Seeing him already rock hard and leaking did something to Dean. He leaned forward, lips hovering just above the other man’s mouth. “Do you think about my lips wrapped around your cock, Cas? Do you think about fucking into my mouth while I’ve got my fingers in your ass? I want you to come down my throat while you ride my fingers. Do you think you can do that for me, baby?”

Castiel was practically writhing underneath him now. “Dean, _yes_. Please. Please do that. Now. I need you, Dean.”

He kissed Cas hard. “Yeah, baby. I need you, too.” Grabbing the lube from the bedside table, he moved down the bed, spreading Cas’ legs apart and settling his ankles on his shoulders. Dean kissed down along his abdomen. “I’ve wanted to do this for so long, Cas. I’ve wanted you in my mouth, wanted to be in yours. There are so many ways I want to make you come, baby.”

Castiel glared up at him balefully. “So stop talking and make me, _baby_.” His dick twitched in response. Who knew that Cas being a sarcastic little shit was a turn-on? Dean poured some lube into his hand.

He circled his fingers around the head of Cas’ cock then took it into his mouth, swirling his tongue along the slit. He lapped gently at the head, then up and down the shaft, pausing to suck experimentally here and there, noting which parts elicited the most twitches, the breathiest responses.

He cupped his lips around just the head and sucked hard, anticipating the buck of Castiel’s hips up into his mouth and using that momentum to swallow him down completely, nose touching the downy hair at the base. He stayed there for a moment, letting Cas feel him swallow around his cock before coming back up.

He moved a hand up along the shaft, starting a rhythm as his other hand circled the tight little hole. “Is this what you want, Cas? You want my fingers? Or do you want this?” His tongue swept a hot line along the cleft of Castiel’s ass, then swirled around the entrance. Castiel moaned loudly. “What do you want, Cas, my tongue or my finger?”

Castiel wasn’t sure which way to move his hips: upwards into Dean’s still-stroking fist, or downward onto his tongue. The sensations were so intense everywhere. “Both. I want both.”

Dean smiled. “Kinky bastard. I like it.” He made a seal around the entrance and sucked, his tongue lapping at the hole. When Cas cried out he did it harder, darting his tongue just inside, greedily taking in every sound. He moaned loudly, letting the sound reverberate through Castiel ass, making him jerk his hips downward.

“More Dean. Give me more.”

Dean pulled his tongue out slowly, licking all the way up Castiel’s balls, pausing for a moment to take each one into his mouth, sucking gently, then moving upwards and sucking down hard on his cock. His other hand moved to Cas’ already slick entrance and he pushed one finger in slowly.

Castiel moaned loudly and pushed his hips down, taking Dean’s finger in all the way. “More.” Dean added a second finger, then a third, scissoring him open while his other hand and mouth kept up a steady rhythm on his cock.

Dean was looking up at Cas through his lashes, admiring how fucking _wrecked_ the blue-eyed former angel looked when a phone started ringing. He pulled off Cas with a slick pop, but didn’t stop either of his hands. “Answer it.”

Cas didn’t even look like he could form a coherent word, much less a conversation, but he answered the phone anyway. He put it on speaker.

“Betty.” It came out as a breathy whine.

“Oh, good! I _am_ interrupting!” Dean could almost hear the wicked smile through the phone. He gave a grin of his own before taking Castiel completely into his mouth and down his throat, really happy that he’d lost his gag reflex a long time ago.

“Ngh!” Dean had crooked his fingers, finding Cas’ prostate. He nearly came off the bed.

Betty’s voice went low. “Oh, my sweet boys, I wish I could be there to see this right now. I want to watch him swallow you down. Are you going to fuck his mouth?” Dean moaned at the thought, sending the vibrations straight into Castiel’s cock, whose hand suddenly gripped Dean’s hair hard, forcibly moving his head up and down.

Cas whimpered. “Betty, I need to let you go.”

“Mm, I’m sure you do. What I wouldn’t give to watch you two. I’ll bet he’s pulling out all the stops on you, sweetheart. Is he using those long fingers to work you open?” Her voice dropped lower. “Do you like it when he talks dirty to you? Do you like the filthy words that come out of his mouth right before you plug it up with your cock?”

The only response Betty got was a breathy whine. “All right, my sweet darlings. I’ll let you enjoy yourselves. Call me if you need me. Kisses!”

“Goodbye.” Cas hung up the phone and flung it across the room. With one hand still working Dean’s head, his other traced the seal of Dean’s lips around his cock. “Dean, I would like to come in your mouth, and then I want you to fuck me.”

Oh, praise to all the gods that existed for Betty. Dean groaned an “mmhmm” around Cas and worked his fingers in and out of the tight hole.

Castiel gripped Dean’s hair tightly and experimentally snapped his hips upward. Dean’s mouth went slack, letting Cas fuck his mouth and down his throat. He could feel the head hitting the back of his throat and swallowed, pulling the leaking length in deeper. All he wanted was to make Cas feel good. He timed the movement of his fingers with the thrusting and very soon felt Cas grow harder and his balls tighten up. He knew the other man was going to come soon. His fingers stayed on Cas’ prostate, pressing down on the spongy surface, and suddenly with a wordless cry Dean’s mouth was being filled up. He couldn’t swallow it all and some of it dripped down his lips and onto his chin like Cas was marking him, claiming him. Fuck, it was hot.

He helped Cas ride through the orgasm before pulling his fingers out. Slicking up his own cock, he lined himself up and slowly pushed in. Dean groaned as Cas’ heat surrounded him. “Holy fuck, baby, you’re so tight.” He pushed in another experimental inch, watching Castiel’s face intently for any sign of hurt or discomfort. There was none; Cas’ head was thrown back, mouth hanging open with breathy whimpers escaping.

Castiel pushed down, pulling Dean in until he was bottomed out. Dean leaned forward and rested his forehead against Cas’, letting the other man adjust. He brushed their mouths together, nibbling at Cas’ bottom lip. “Tell me when I can move, baby. Tell me when it feels good.”

Castiel nodded. “It feels good, Dean.”

Dean pulled back an inch then pushed in again. “Fuck. Baby, you’re so tight.” He pulled back again slowly, pushing in even more gently, taking a long time before he set a pace he was sure wouldn’t hurt Castiel. What was supposed to be a hot and fast round two turned into a slow burn, building leisurely until they were both gleaming in perspiration. He felt Cas grow hard again (did the man have a refractory period?), and trapped it between them, knowing the friction of their movement would be all he would need to come again.

Dean rested their foreheads together, breathing slowly. There was something that felt so good about this, so _right_ , like finally having a place to call home. He grabbed one of Cas’ hands and laced their fingers together.

Their eyes met, held. Dean was overwhelmed by the emotion in them. It started a burning in his chest that spiraled lower and settled low in his belly.

Gradually their pace quickened and Dean dropped his head to rest in the crook of Cas’ neck. He kissed him softly there, whispering, “Cas,” over and over like a prayer. Perhaps it was.

Castiel’s free hand suddenly grabbed at Dean’s shoulder as he gasped out, “Dean. Oh, _oh_ , I’m close.”

Dean kissed him. “I’ve got you, sweetheart. Let go. Let me come with you.” Then Dean was feeling warmth spilling out between them as Cas gave a little sigh. He swallowed the sigh with a kiss and found his own release, going still as Cas clenched around him.

Dean had been to Heaven. This was better.

They lay there for a minute, coming down from their high before Dean gently pulled out and, with a kiss, got up to get a wet washcloth. After cleaning them both up he threw the washcloth somewhere in the vicinity of the bathroom and pulled Cas onto his chest. He pressed a kiss into his hair.

“Sammy’s gone for a while to give us some privacy.”

“That’s very kind of him. Is that okay with you?”

Dean shrugged. “Well, yeah. I mean, I’ll miss him, but it’s not every day you get to actually get together with the guy you’ve been in love with for years.”

Cas’ hand, which had been tracing patterns of Dean’s freckles, went still.

Dean replayed what he’d just said in his head. _Shit_. “I, uh…”

Castiel sat up and placed a single finger over Dean’s mouth. “You’ve been in love with me for years?”

With a finger keeping his mouth closed, Dean could only nod. Cas regarded him. “Every time we are in the same room together, I am slightly nervous. I feel flush. Sometimes it is difficult to break eye contact with you. I think about you whenever we’re not together, and sometimes it causes a pain in my chest. I can’t sleep sometimes because you’re on my mind. When I feel like you’re mad at me I get so worried that I can’t eat. But every time you touch me that all goes away and I feel strangely calm. Is that love?”

Dean nodded and kissed the finger still over his mouth before turning his head. “Yeah, Cas. That’s love.”

Castiel regarded him. “Then I have been in love with you for years, as well, Dean Winchester.”

A knot that Dean didn’t know was in his chest loosened. He sat up and gently kissed away the longing and pain of the last several years. Yes, this was definitely better than Heaven.

“Good. Now enough with the chick flick moment, Cas. Sammy brought breakfast.”

 


	3. Chapter 3

**Summary for the Chapter:**

> “That’s it, Dean. You look so lovely when you choke yourself trying to swallow me down. Just picture how good it will be when you feel me pushing inside you from behind. You’ll feel so good around me, so hot and tight. Come on, my good boy, just a little deeper. There we go.”

Betty pressed ‘end’ on the phone and tapped it against her lips thoughtfully. She liked Castiel. He was straightforward and honest about his desires, which could be used to everyone’s advantage. Dean was usually quiet about what he wanted unless he was made to beg for it, but once he got going, his dirty talk was a thing of beauty. It wouldn’t take much coaching on Betty’s part before Castiel was ready to play Dean like the beautiful instrument he was.

After a moment, she sent off a text to Castiel, asking for them to meet up if he was interested in Dom training.

Outlining a scene that would be appropriate for them in her head, Betty dressed in a dark blue pantsuit with a matching blazer and an open-collared, white shirt. It was expensive to get blazers tailored to fit her busty frame so she didn’t look like a goddamned “Oompa Lumpa”, but in the corporate world she couldn’t afford to go running around in the rockabilly dresses she preferred. The illusion of power was more compelling than how much power a person actually held. And Betty held a lot of power, but she was able to make almost anyone believe she possessed so much more.

Her meeting at work today would bring in enough money that she could spend at least a month concentrating on her subs—her real work. For that reason she was willing to put on the god-awful suit and curb her language for an afternoon.

Checking her bright red lipstick one more time in the mirror, Betty grabbed her purse and keys from the side table near the door and headed to Sandover, Inc.

 

o.O.o

The wait in the lobby lasted less than five minutes. Betty smiled to herself as the door to the conference room opened and a woman walked towards her. You could always judge the importance of someone by how long they were kept waiting. She had obviously made a good enough impression to warrant a high status already.

The smile, however, died on her lips as the woman approached. She was maybe five years older than Betty—early thirties to her late twenties—and her long hair was almost the exact shade as Betty’s own. She had large, hazel eyes and a mouth that seemed prone to smiling. She wore a bright blue blazer over a black t-shirt emblazoned with the Slytherin crest, and the khakis she wore seemed to be her only concession to a professional wardrobe.

Holding a hand out and smiling widely, the woman said, “You must be Ms. Days. I’m Charlie Bradbury, head of IT. Pleasure to meet you.”

Betty looked at the hand for a moment before taking it in her own. She squeezed gently and let her fingers drift down over the pale skin on her wrist. Meeting Charlie’s eyes, she winked and murmured, “The pleasure, I assure you, Charlie, is all mine.”

It was worth losing a bit of professionalism to see the pink alight on Charlie’s cheeks. Her answering smile was soft, but her words belied her demure expression.

“Well, Ms. Days, let’s see if we can’t change that by the end of the day.” Oh yes, she was positively wicked. Betty decided she was going to have fun with this one.

“Perhaps we can start with you calling me Betty. Then we can move on to, say, dinner?”

Those big hazel eyes widened further on a delighted smile. “Well, Betty, let’s see how the meeting goes first, then I’ll let you know.”

“Looking forward to it.”

This day was getting better by the minute.

 

o.O.o

Later that evening, after a _very_ successful meeting at Sandover, the phone number of one Charlie Bradbury, and the promise of a date within the next week, Betty heard back from Castiel. He was interested in understanding the ins and outs of the dom/sub dynamic so he and Dean could continue to have it as part of their own relationship.

The next day Castiel was at Betty’s apartment, sitting on the couch amongst a pile of binders, ropes, whips, paddles, clamps, belts, gags, dildos, butt plugs, and vibrators. He was a sponge, soaking up every piece of information Betty pressed upon him, always attentive and serious.

After an entire afternoon of instruction, Betty laid out what she thought would be a safe enough scenario to start Castiel out. She insisted on being present for his first scene so as to be able to give moral support—that and the fact that they were the most attractive couple she’d had the pleasure of working with in years. She had no intention of letting them go with only one scene.

“I want to see what you’re capable of, Castiel,” Betty said. “Use me as you see fit. My safeword is hypothalamus.”

Castiel’s lips pulled up, almost a smile. “The area of the brain responsible for the sex drive. Clever.”

Of course it was clever.

They agreed to meet again on Friday night at a hotel of Castiel’s choosing. Betty let him out of her apartment, proud of what they’d accomplished in a single day and very much looking forward to the conclusion of his training.

A scene on Friday, a date on Saturday. What could be better?

 

o.O.o :: o.O.o

Castiel wasn’t precisely nervous for leading his first scene, but he couldn’t think of a better word to describe his emotions should someone ask. It was yet another thing to get used to, one more difficulty that came hand in hand with humanity.

Betty had knocked on the door twenty minutes ago, long after he and Dean had arrived and settled in. Dean had even gone so far as to give him a back rub to calm his nerves. It had ended with Castiel on his back with Dean coming down his throat, but it had released a good deal of tension nonetheless.

The room they were in was large and clean with a king-sized bed and extra pillows. Betty had brought all rules and limits in writing, and all parties had gone over them and given consent. Now Dean was on his knees on the floor—a position that was able to get Castiel hard without even trying—and Betty was standing next to the bed. They awaited his pleasure to start the scene.

Castiel turned his back on them for a moment and took three slow, deep breaths. It felt like pulling on his old mantle of power and condescension from when he was first assigned to drag Dean Winchester out of Hell. The biggest differences were that he knew about—and desired—the sexual pleasure that could be attained, and the fact that this time Dean was the one taking orders from him. He tucked his ‘self’ in the back of his mind and turned around as a Dom.

His eyes raked over Dean where he was kneeling, drinking in the sight, still barely letting himself believe that after all this time he finally had what he wanted. While Dean’s posture was demure with his hands clasped gently behind his back, his eyes were hungry, as though he could devour Castiel with just a look. A thrill of power shot through him at the thought.

“Dean, I want you to undress yourself, then Betty. You may not seek to bring any pleasure to either of you while you do so. You will not be touched until you beg for it.”

Castiel could see the shiver that ran through Dean’s body at the command. Yes, the man kneeling before him, while normally so used to taking charge and being in control, willingly ceded that control to himself, and obviously took great pleasure in doing so. It was now completely in Castiel’s hands to give Dean and Betty as much pleasure as he possibly could. He would not let them down.

Dean quickly and efficiently undressed himself, neatly folding his clothes and leaving them in a pile next to the bed. Castiel forced himself to stillness as more of Dean’s skin became visible, even though all he wanted to do was put his mouth on every inch of skin he could find.

When Dean moved on to Betty, she met his eyes and quirked an eyebrow, almost daring him to brush his fingers—or his erection—over her body. She arched her back when he unhooked her bra, let her breath catch in her throat when he slid it off her shoulders along with her dress. When she stepped out of it, he picked up the dress and folded it, setting the pile next to his own. Castiel did not miss these little defiances and took note of them for later.

Dean turned back towards Castiel, posture once again submissive but keeping direct eye contact. Betty, on the other hand, stood proudly: legs apart, shoulders back, and inquisitive eyebrow raised; a direct challenge to Castiel to prove his worthiness of taking care of Dean Winchester. He met her eyes steadily, not worried about whose gaze would falter first. Castiel may be human now, but he had been an Angel of the Lord. He would not break before her.

After a moment, Betty dropped her eyes. He allowed himself a single, straight-faced breath to enjoy the victory before meeting Dean’s eyes again and pointing to the bed. “Get on the bed, hands and knees, facing me. Betty, get behind him. You will find several items in the bedside drawer. Take them out.”

Unhurriedly, Castiel began removing his own clothing as Betty removed several items from the drawer. She laid them out next to her in ascending order of size, then impassively looked at him again. It would take more than a single staring contest to break her, he knew.

Dean’s breathing was getting harsher the more clothes Castiel removed. He wanted so badly to reach out and stroke the perfect lips of the man he had desired for so many years, but managed to maintain his discipline. This night was not about Castiel. This night, every night, was about Dean.

Once he was fully naked, Castiel put one hand on his cock and stroked it lightly, watching Dean’s eyes track the movement. “Dean,” he said, “I want you to let Betty open you up. Betty may start with the smallest and work her way up. She may not touch you in any way with her own body.”

Castiel could practically feel the pride rolling off Betty in waves. He must be doing well so far according to her very exacting standards. He waited until she had uncapped the lube and was just beginning to drizzle the clear liquid onto his puckered hole to speak again. “Dean, you will suck on my cock while she opens you up. You may only touch me with your lips and tongue.”

Dean’s lips had just wrapped around the head of Castiel’s cock when Betty inserted the first dildo, which was only about an inch in diameter. She pushed it in halfway and began gently fucking him with it, adding more lube as needed. He moaned while his head bobbed up and down, trying desperately to take all of Castiel into his mouth that he could without the use of his hands. Good boy.

“That’s it, Dean. You look so lovely when you choke yourself trying to swallow me down. Just picture how good it will be when you feel me pushing inside you from behind. You’ll feel so good around me, so hot and tight. Come on, my good boy, just a little deeper. There we go.”

Castiel stood very still, careful to not thrust into Dean’s mouth, to allow Dean to do only as much or as little as he desired while Betty slowly moved up to the second and then the third toy. A couple minutes with the third one—three inches in diameter—should be all that Dean would need to be ready to take him.

The sight of Dean’s lips wrapped skillfully around his engorged member nearly undid Castiel. He had fantasized about moments like this for years, never daring to believe they could happen, but wishing just the same. Watching Dean—chest flush, his cock red and dripping pre come—push back against the dildo in Betty’s hand, taking himself deeper while moaning around Castiel’s cock made a thrill shoot down his spine. He began to understand why Betty and Dean had gotten into this in the first place. The play of power, of giving and receiving, was a heady thing.

Castiel was very carefully not looking at or acknowledging Betty. To do so would be to give back some of the power she was used to holding in these situations, and Castiel knew better than most how to treat someone who had previously been a superior until they bent to the role of subordinate.

Castiel could see by her dilated pupils and the rapid rise and fall of her chest that Betty was quite aroused. There was a great likelihood that she was used to denying herself pleasure while seeking it for her subs, but at the moment she had no control over her actions. Being at Castiel’s whim, not allowed to seek any stimulation, would be an almost overwhelming change of pace for her. Castiel waited a minute longer, letting the tension build, before truly beginning to break down Betty’s walls.

He took a slow step back, pulling his cock out of Dean’s mouth with a wet pop, watching it twitch with interest as a trail of saliva still connected them. He wanted nothing more than to take Dean’s mouth with his own and plunge his tongue inside, but Dean hadn’t asked yet, hadn’t begged prettily, so Castiel needed to maintain his composure. He reminded himself that this was not about taking what he wanted, but giving Dean and Betty exactly what they asked for.

“I think that’s enough for now. I want you to turn around and show me that pretty pink hole that I’m about to fuck. Let Betty lie underneath you while I spear you open, but you may not make contact. She is not to be touched.” Castiel knew that talking about her as though she weren’t there, making her get her instructions second-hand, would be infuriating to Betty. Good. Fury was a passion, and building it up as much as he built her arousal would make for such a satisfying submission when she finally surrendered.

o.O.o :: o.O.o

Dean wasn’t sure he’d ever been this turned on in his life. He knew exactly what Cas was doing, the mind games he was playing with Betty, and watching the fine tremors go through her body as she attempted to resist were just fucking gorgeous. If he were the one Cas was treating that way, he’d have given in a long time ago. But Dean’s greatest asset as a sub was his desire to do whatever it took to please his Dom. He loved it when he was called a “good boy”, when he got a touch or a look in praise, when he could give his Dom pleasure.

He shivered in anticipation when he felt the bed dip behind him and the head of Castiel’s condom-covered cock brushed against his entrance. He held his breath, waiting for the fullness to penetrate him, but it didn’t happen. Cas just stood there, _right fucking there_ , but wasn’t doing anything. What the fuck?

Oh. _“You will not be touched until you beg for it.”_

“Castiel,” he whispered, pushing his hips back. Dean hadn’t been told that he needed to call Cas ‘sir’, but he figured he was safer using his whole name. “Please. I need you. Please, Castiel.”

He heard Cas’ breath hitch, and then, mercifully, there was a hand running along his spine lovingly. “That’s my good boy, Dean. I knew you could do it. Come on, you’re going to fuck yourself on my cock. Nice and easy, I’ve got you.”

Dean looked down, met Betty’s eyes. She was trying so hard to resist, but he could tell that his own begging had done something to her. It always had. She was getting closer to giving in, and Dean couldn’t wait to see what would happen when his cool, collected Betty Days broke apart.

He winked at her as he pushed himself back, guided by Cas’ hand on his hip. He gasped when the head breached his entrance. Even stretched out as he was, it burned, impaling himself on Cas’ cock. “Oh, fuck yes, Cas,” he moaned, pushing himself back further. The hand that had been stroking his hip vanished, and Dean replayed what he’d said. “Shit. Castiel. I’m sorry. Castiel. Please, touch me.” He sighed in relief when the hand returned and gently pressed against his skin.

Moving slowly, Dean kept rocking back a little at a time until his ass was flush against Cas’ hips, encouraged by the murmured, “Yes, Dean. Good boy. A little more, that’s it,” coming from Cas. He paused for a moment, letting himself adjust around the thickness of Cas’ cock, and watched Betty as he started fucking himself slowly.

Her head was thrown back, hands twisted tight in the sheets in an effort to keep her hands to herself. Betty loved to touch, to have that physical control, and it must be a goddamn trial to resist, only able to listen to the sounds of Dean fucking himself hard and fast. It was taking a lot of effort on his part to not stroke his own dick, or caress the fucking gorgeous breasts underneath him. He wanted to bury his face in her pussy and lick and suck until her juices dripped down his chin. He wanted to bury his cock inside her while Cas fucked him from behind.

Castiel began kneading Dean’s ass as it was pounding back onto him, and Dean picked up the pace. He knew it wouldn’t be too much longer before Cas came, and then Dean would get more than a little bit of touching. Remembering how much dirty talking had worked over the past few days, Dean threw himself back on Cas’ cock and moaned, “Fuck, yes, Castiel, you feel so fucking good in my ass. Want you to come, baby, come so hard from me riding your cock.”

Dean knew Cas was about to come by the way he grabbed his hips and slammed Dean back against him. After only a few more thrusts, Cas pulled out, ripped the condom off, and came on Betty, leaning his head down against Dean as the thick white ropes spattered across her stomach and breasts. Dean’s dick gave an interested twitch at the moan that escaped Betty’s bright red mouth. He really wanted his cock against that tongue.

Castiel kissed Dean’s spine and patted him on the hip, indicating that he wanted Dean to move over. When the two men were standing next to the bed, Castiel stared at Betty. She squirmed. Yeah, Dean really wanted to fuck her right now.

“Betty, tell me what you want,” Castiel’s soft voice belied his hard and impassive face.

She stared at Castiel for a long moment before Dean saw her resolve collapse. “Please,” Betty whispered brokenly, arching up and keening as her orgasm slammed into her. Dean had known that it would take the breaking down of her defiance to push her over the edge. Her natural state was not one of submission, and letting go of that control—giving someone else total power over her—must have been a terrifying thrill. Dean was right; seeing Betty Days come undone was a beautiful sight. He shivered in anticipation of what would come next.

Castiel climbed up on the bed and straddled Betty’s waist. He rubbed his come into her skin, massaging gently, all the while telling her what a good girl she’d been. Dean wanted to stand there and fist his cock while Cas fucked her, he wanted to bury himself into her wet heat, wanted to listen to the little sighs and moans she was making all day. Instead he stood quietly, hands clasped behind his back until Cas told him what to do.

Once Castiel had finished rubbing his come in, he pulled Betty up to sitting and lightly pressed a kiss to each cheek. “You defied me twice, Betty. I’m going to punish you for that now, and then we’re going to take care of you. You’ve been doing such a good job. Can you take your punishment?”

Betty nodded, breath still coming in hard gasps. She turned onto her hands and knees, and shuddered when Castiel asked for Dean to go get the paddle out of the bag.

“I’m going to spank you twice for each time you defied me. I want you to count them. Can you do that for me?” Castiel’s voice was a soft murmur as he rubbed his hand soothingly over Betty’s ass.

She nodded and put her face into the comforter. Dean’s own skin tingled when the first _whack_ filled the air. He could almost feel the delicious pain and wished he were the one laid out for Cas, ass cheeks turning an appealing shade of pink.

Betty counted out all four spankings, tears gently rolling down her cheeks by the end. Cas set the paddle aside and gathered her up into an embrace, telling her how good she was for him, how he knew she could do it. Then he asked her to lay down on her back and gestured for Dean to kneel up by her head.

“Dean, you may not come yet, but I want you to touch her.” Then Cas laid down on his stomach, pulled Betty’s legs apart, and licked her clit.

If Dean had thought watching Cas rub his come into Betty was hot, it was nothing compared to watching him eat her out. His pink, chapped lips ravished her pussy while he slipped two fingers inside and massaged her inner walls. He hummed around her clit, licked it in broad stripes, and sucked on it until Betty was a moaning, writhing mess beneath him. Dean had almost forgotten that he was able to touch now.

He leaned over and kissed his way down her neck to her collarbone, where he paused to lick and suck while he stuck two fingers in her mouth. When Betty had thoroughly sucked on his fingers and gotten them wet, he took them out of her mouth and rolled her nipples between his fingers. She arched her back saying, “Oh, yes, Jesus fucking Christ, Dean, _yes_.”

He replaced his fingers with his mouth, licking and sucking on each nipple like he wanted to do with her pussy. He gently nipped at each one and moaned at the thought of shoving his rock-hard and dripping cock down her pale throat.

Castiel paused and looked up, his lips slick and shiny with Betty’s arousal. “What do you want, Dean?”

Dean looked down at Betty, picturing how she’d look from this angle with her lips wrapped around his dick. He used to love her mouth, and having already had Cas blow him once today, he wanted to see if she could take as much of him in her mouth as the former angel. “I want her to suck my cock, Castiel. Please.” Throwing around that word seemed to have a special effect on Cas, because he smiled.

“All right. You may let her suck on you while you get me hard again, but you can’t come yet. Only I can make you come.” Dean nodded his assent, not bothering to suppress the shiver those words sent down his spine.

“Fuck, yes,” Dean said, and rubbed the head of his cock over Betty’s lips, which opened eagerly.

With a murmured, “Come on, sweet boy,” she swallowed him down and began working her lips and tongue all over his cock. It took a great deal of effort not to come immediately from the intense pleasure surging through his neglected dick.

Castiel scooted closer to Dean, two fingers still inside Betty and his thumb rubbing her clit. He brought his other hand up to cup Dean’s face and press kisses everywhere. “Such a good boy, Dean,” he whispered between kisses, tongue darting out to part Dean’s lips. Dean returned the kiss with all the longing he’d felt at not being able to touch Cas.

Castiel cupped Dean’s throat gently and rubbed his cheek with his thumb. “I’m going to fuck you one more time, and then after my come is coating the inside of your ass, I’m going to let you come down my throat. I need you to hold on that long for me, Dean. I know you can do it. You’re such a good boy.”

Dean felt a surge of pride at hearing how well Cas thought he was doing. He wanted to be really worthy of that praise, though, so he pushed his hips down, shallowly fucking in and out of Betty’s mouth, getting himself as close to the edge as possible without tipping over. It was tough; her tongue was just as wicked as he remembered. But he had Cas to prove himself to, and Dean wasn’t going to let him down.

Castiel maneuvered himself so Dean would have an easier time sucking his cock. Cas put his free hand on Dean’s head and guided it up and down. His other hand was now three fingers deep in Betty, who was rolling her hips down onto them while her mouth hung open, letting Dean fuck his way down her throat. She ran a hand up the cleft of his ass and circled his still loose hole. He moaned loudly, sending the vibrations through Castiel, who was almost completely hard again.

Suddenly Dean’s throat was empty and he was being picked up and moved on top of Betty. His mouth went dry at the sheer strength Castiel casually showed. He heard a condom wrapper tear, then felt Castiel roll the condom down Dean’s length and give it a couple of strokes.

Dean felt lips at his ear. “Fuck her, Dean. But remember, don’t come.”

He bent Betty’s knees up until she was almost folded in half, then sank deep within her in one thrust. He waited, knowing that any moment—

Castiel grabbed Dean’s hips and slammed inside, fucking him at a hard, fast pace, not giving him any time to adjust. He was barely able to move himself at all, mostly fucking into Betty from the force of Cas ramming his cock all the way into Dean.

Dean’s senses were overwhelmed. With Betty underneath him keeping up a litany of _yes, fuck, yes, come on, fuck me_ , and Castiel hitting his prostate with every other thrust, it took every ounce of control he had not to come. Thankfully, only a couple of minutes passed before Betty was shuddering around him, and he was able to pull out and take the condom off while she caught her breath.

Cas had his hands everywhere. Tweaking Dean’s nipples, running up and down his side, stroking his cock occasionally. Just when Dean was sure he couldn’t stave off his own orgasm anymore, Cas grabbed Dean’s hips and stilled, pulsing his come deep inside of Dean. When he pulled out, Dean was empty for only a moment before he felt a plug enter him, the tip resting against his prostate and keeping Cas’ come deep inside him.

Then Dean was standing, looking down at Cas, who was on his knees. Castiel looked back up at him with those fucking blue eyes. “Come for me, Dean,” he whispered, before swallowing him down in one go. That was all it took; Dean’s over-sensitive cock pulsed down Cas’ throat as his hands threaded through his hair.

Dean collapsed on the bed next to Betty, who moved until she was able to rest her head on his chest. Cas disappeared for a moment, returning with a jar of ointment in his hand. He kissed them both on the forehead. “You were both so good for me,” he said, a wide smile on his face. “I have ointment for you, Betty, if you could turn just a bit.”

Dean smiled as he watched Cas carefully apply the ointment to Betty’s pink flesh. When he was done, Cas knelt between Dean and Betty and ran his hands up and down their backs soothingly. “Is there anything I can do for you?”

Dean grinned. “Naw, babe, you were wonderful. Sleepy time now.”

Betty chuckled. “For you, maybe. I need to get dressed and head home. I have a date tomorrow that I need to pick an outfit out for.” She got up and began gathering her things.

“Oh yeah? Is she hot?”

Betty nodded. “Very. Red hair, wicked smart. Head of IT at Sandover.”

Dean blinked. “Charlie? You’re having a date with our Charlie?”

“How do you know her?”

“Oh, she’s helped us out of a scrape or two,” Dean hedged. “Have fun with her. And brush up on your Harry Potter and Star Trek trivia before you go.”

“Will do.” Betty gave Dean a kiss on the cheek, then turned towards Castiel. “You did very well. I’m proud of what you accomplished in such a short amount of time. Not many people would have been able to get me to submit.” She kissed his cheek. “You boys keep in touch. Be good to each other.” She walked out the door, letting it click shut gently behind her.

Castiel turned to Dean. “Are you in agreement? Was I … satisfactory?”

Dean pulled Castiel’s head to his chest and kissed his hair. “Cas, you were fantastic. We’re going to spend a lot of time doing this. I just have one request.”

“Anything.” Castiel’s response was immediate.

“Can we take a nap, and then order some pie?”

Cas’ eyes crinkled as he smiled and kissed Dean. “Of course.”

**Notes for the Chapter:**

> There we are, my lovelies! I hope you enjoyed the conclusion to this little trilogy. There will be a follow-up one-shot with Betty and Charlie's date. It won't contain Dean and Cas at all (or if it does, they'll just be side characters). You can find me on tumblr at tumblr.com/blog/eveanyn.

**Author's Note:**

> I hope you liked it! As I mentioned, it's my first fic, so comments are welcome.
> 
> Find me on my tumblr, [Eveanyn.](http://eveanyn.tumblr.com/)


End file.
